HUE025982T2 - New polymorphic forms of perindopril (L) -arginine and a process for their preparation - Google Patents

New polymorphic forms of perindopril (L) -arginine and a process for their preparation Download PDF

Info

Publication number: HUE025982T2
Authority: HU; Hungary
Prior art keywords: perindopril; arginine; ind ind; solvent; preparation
Prior art date: 2008-06-24

Application number

HUE09769810A

Other languages

English (en)

Hungarian (hu)

Inventor

Ramakoteswara Rao Jetti

Chetan Kanaiyalal Raval

Ramireddy Bommareddy Aggi

Debashish Datta

Original Assignee

Mylan Laboratories Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2008-06-24

Filing date

2009-06-22

Publication date

2016-05-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=41203736&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=HUE025982(T2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2009-06-22 Application filed by Mylan Laboratories Ltd filed Critical Mylan Laboratories Ltd

2016-05-30 Publication of HUE025982T2 publication Critical patent/HUE025982T2/en

Links

238000000034 method Methods 0.000 title claims description 70
238000002360 preparation method Methods 0.000 title claims description 57
230000008569 process Effects 0.000 title claims description 57
RYCSJJXKEWBUTI-YDYAIEMNSA-N perindopril arginine Chemical compound OC(=O)[C@@H](N)CCCNC(N)=N.C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 RYCSJJXKEWBUTI-YDYAIEMNSA-N 0.000 title description 188
IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 claims description 93
229960002582 perindopril Drugs 0.000 claims description 92
239000002904 solvent Substances 0.000 claims description 57
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
239000002253 acid Substances 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 22
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 15
238000002955 isolation Methods 0.000 claims description 13
239000000725 suspension Substances 0.000 claims description 10
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 8
238000001816 cooling Methods 0.000 claims description 8
239000000843 powder Substances 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 2
150000002430 hydrocarbons Chemical class 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 2
230000007928 solubilization Effects 0.000 claims 2
238000005063 solubilization Methods 0.000 claims 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
ODKSFYDXXFIFQN-SCSAIBSYSA-N D-arginine Chemical compound OC(=O)[C@H](N)CCCNC(N)=N ODKSFYDXXFIFQN-SCSAIBSYSA-N 0.000 claims 1
229930028154 D-arginine Natural products 0.000 claims 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
125000000129 anionic group Chemical group 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 claims 1
229910052796 boron Inorganic materials 0.000 claims 1
230000014509 gene expression Effects 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000000178 monomer Substances 0.000 claims 1
238000010792 warming Methods 0.000 claims 1
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical class OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 57
239000000243 solution Substances 0.000 description 47
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000007787 solid Substances 0.000 description 22
239000012296 anti-solvent Substances 0.000 description 20
238000000634 powder X-ray diffraction Methods 0.000 description 18
238000010992 reflux Methods 0.000 description 17
239000003960 organic solvent Substances 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
238000003756 stirring Methods 0.000 description 11
238000001907 polarising light microscopy Methods 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
239000004475 Arginine Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
229930064664 L-arginine Natural products 0.000 description 7
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 7
235000009697 arginine Nutrition 0.000 description 7
230000009477 glass transition Effects 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000001144 powder X-ray diffraction data Methods 0.000 description 6
239000002002 slurry Substances 0.000 description 6
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical class CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
229960003076 perindopril arginine Drugs 0.000 description 5
239000000047 product Substances 0.000 description 5
238000004626 scanning electron microscopy Methods 0.000 description 5
238000001694 spray drying Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
150000001483 arginine derivatives Chemical class 0.000 description 4
238000010533 azeotropic distillation Methods 0.000 description 4
238000010586 diagram Methods 0.000 description 4
238000000113 differential scanning calorimetry Methods 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
238000004821 distillation Methods 0.000 description 4
150000004677 hydrates Chemical class 0.000 description 4
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
IYNMDWMQHSMDDE-MHXJNQAMSA-N perindopril erbumine Chemical class CC(C)(C)N.C1CCC[C@@H]2N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H](C(O)=O)C[C@@H]21 IYNMDWMQHSMDDE-MHXJNQAMSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 3
235000014852 L-arginine Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 3
108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
239000002245 particle Substances 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
-1 dichloroform Chemical compound 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
150000002688 maleic acid derivatives Chemical class 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000009466 transformation Effects 0.000 description 2
238000013519 translation Methods 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
KFUSEUYYWQURPO-UHFFFAOYSA-N 1,2-dichloroethene Chemical compound ClC=CCl KFUSEUYYWQURPO-UHFFFAOYSA-N 0.000 description 1
YVCVYCSAAZQOJI-JHQYFNNDSA-N 4'-demethylepipodophyllotoxin Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YVCVYCSAAZQOJI-JHQYFNNDSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
229940062352 aceon Drugs 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
238000013459 approach Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
238000001938 differential scanning calorimetry curve Methods 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000001788 irregular Effects 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
238000000386 microscopy Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000011146 organic particle Substances 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
229960003929 perindopril erbumine Drugs 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
238000010926 purge Methods 0.000 description 1
239000002964 rayon Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000001878 scanning electron micrograph Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002076 thermal analysis method Methods 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000000844 transformation Methods 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000009777 vacuum freeze-drying Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

HUE09769810A 2008-06-24 2009-06-22 New polymorphic forms of perindopril (L) -arginine and a process for their preparation HUE025982T2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IN1535CH2008		2008-06-24

Publications (1)

Publication Number	Publication Date
HUE025982T2 true HUE025982T2 (en)	2016-05-30

Family

ID=41203736

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HUE09769810A HUE025982T2 (en)	2008-06-24	2009-06-22	New polymorphic forms of perindopril (L) -arginine and a process for their preparation

Country Status (13)

Country	Link
US (3)	US8686161B2 (fr)
EP (2)	EP2682388B1 (fr)
AU (1)	AU2009263737B2 (fr)
CA (2)	CA2729604C (fr)
CY (1)	CY1116930T1 (fr)
DK (1)	DK2318365T3 (fr)
ES (1)	ES2552653T3 (fr)
HR (1)	HRP20151208T1 (fr)
HU (1)	HUE025982T2 (fr)
PL (1)	PL2318365T3 (fr)
PT (1)	PT2318365E (fr)
SI (1)	SI2318365T1 (fr)
WO (1)	WO2009157018A2 (fr)

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Publication number	Priority date	Publication date	Assignee	Title
FR2897866B1 (fr)	2006-02-28	2008-04-18	Servier Lab	Forme cristalline alpha du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent
DK2318365T3 (en)	2008-06-24	2015-11-23	Mylan Lab Ltd	NOVEL polymorphic forms of perindopril (L) -arginine AND PROCESS FOR PREPARATION THEREOF
AU2009212902A1 (en) *	2008-09-03	2010-03-18	Apotex Pharmachem Inc.	Amorphous form of an L-arginine salt of perindopril and processes of preparation thereof
FR2985511B1 (fr) *	2012-01-05	2014-01-03	Servier Lab	Forme cristalline delta du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent
FR2985512B1 (fr) *	2012-01-05	2014-06-20	Servier Lab	Procede de preparation du sel de l-arginine du perindopril
CN103172696B (zh) *	2012-12-19	2014-12-17	宁波美诺华药业股份有限公司	一种γ晶型的培哚普利精氨酸盐的制备方法
WO2016178591A2 (fr)	2015-05-05	2016-11-10	Gene Predit, Sa	Marqueurs génétiques et traitement de l'obésité masculine
PH12018502155B1 (en)	2016-04-20	2024-03-27	Servier Lab	Pharmaceutical composition comprising a beta blocker, a converting enzyme inhibitor and an antihypertensive or an nsaid
CN109725022A (zh) *	2018-12-27	2019-05-07	湖南科技大学	一种结合水含量的快速测量方法
EP3842035A1 (fr)	2019-12-23	2021-06-30	KRKA, d.d., Novo mesto	Composition pour la préparation de granulés de périndopril arginine, procédé pour leur préparation et composition pharmaceutique comprenant les granulés
CN112047999B (zh) *	2020-09-18	2022-12-02	天津力生制药股份有限公司	一种γ晶型的精氨酸培哚普利盐的制备方法
SI26268A (sl) *	2021-11-18	2023-05-31	Zupet Rok	Postopek za pripravo hidratirane oblike perindopril l-arginina
CN114149357B (zh) *	2021-12-29	2024-06-25	江苏嘉逸医药有限公司	一种γ晶型培哚普利精氨酸盐的制备方法

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US4616030A (en) *	1979-12-07	1986-10-07	Adir	Perhydroindole-2-carboxylic acids as antihypertensives
US4508729A (en)	1979-12-07	1985-04-02	Adir	Substituted iminodiacids, their preparation and pharmaceutical compositions containing them
US4616031A (en) *	1979-12-07	1986-10-07	Adir	Perhydroindole-2-carboxylic acids as antihypertensives
US5162362A (en) *	1980-08-30	1992-11-10	Hoechst Aktiengesellschaft	Octahydroindole-2-carboxylic acids
DE3226768A1 (de) *	1981-11-05	1983-05-26	Hoechst Ag, 6230 Frankfurt	Derivate der cis, endo-2-azabicyclo-(3.3.0)-octan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung
FR2620709B1 (fr)	1987-09-17	1990-09-07	Adir	Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese
GB9101443D0 (en)	1991-01-23	1991-03-06	Plessey Telecomm	Coin mechanisms
FR2811319B1 (fr) *	2000-07-06	2002-08-23	Adir	Nouvelle forme cristalline beta du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent
FR2811318B1 (fr) *	2000-07-06	2002-08-23	Adir	Nouvelle forme cristalline gamma du sel de tert-butylamine du perindopril, son procede de preparation et les compositions pharmaceutiques qui la contiennent
FR2838648B1 (fr)	2002-04-18	2004-05-21	Servier Lab	Nouveau sel de perindopril et les compositions pharmaceutiques qui le contiennent
US7521566B2 (en) *	2003-02-28	2009-04-21	Les Laboratoires Servier	Process for preparation of perindopril and salts thereof
ATE310012T1 (de) *	2003-08-29	2005-12-15	Servier Lab	Verfahren für die synthese von perindopril und seiner pharmazeutisch annehmbaren salzen
DK1420029T3 (da) *	2003-12-10	2008-06-16	Servier Lab	Fremgangsmåde til syntese af perindopril og farmaceutisk acceptable salte heraf
US7615571B2 (en) *	2004-05-31	2009-11-10	Ipca Laboratories Ltd.	Process for manufacture of pure (2S, 3aS, 7aS)-1-[(2S)-2-[[(1S)-1-(ethoxycarbonyl) butyl]amino]-1-oxopropyl] octahydro-1H-indole-2-carboxylic acid and its tert. butyl amine salt
JP2008545006A (ja) *	2005-07-05	2008-12-11	シプラ・リミテッド	Ａｃｅ阻害剤の合成方法
FR2897865B1 (fr) *	2006-02-28	2008-04-18	Servier Lab	Forme cristalline beta du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent
FR2897866B1 (fr) *	2006-02-28	2008-04-18	Servier Lab	Forme cristalline alpha du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent
EP1864973A1 (fr)	2006-06-09	2007-12-12	Sochinaz SA	Procede de preparation de perindopril et de sels de celui-ci
DK2318365T3 (en)	2008-06-24	2015-11-23	Mylan Lab Ltd	NOVEL polymorphic forms of perindopril (L) -arginine AND PROCESS FOR PREPARATION THEREOF
AU2009212902A1 (en) *	2008-09-03	2010-03-18	Apotex Pharmachem Inc.	Amorphous form of an L-arginine salt of perindopril and processes of preparation thereof
WO2014057404A1 (fr) *	2012-10-10	2014-04-17	Piramal Enterprises Limited	Procédé amélioré de préparation d'un intermédiaire de périndopril

2009
- 2009-06-22 DK DK09769810.4T patent/DK2318365T3/en active
- 2009-06-22 US US13/001,180 patent/US8686161B2/en not_active Expired - Fee Related
- 2009-06-22 CA CA2729604A patent/CA2729604C/fr not_active Expired - Fee Related
- 2009-06-22 PL PL09769810T patent/PL2318365T3/pl unknown
- 2009-06-22 CA CA2919564A patent/CA2919564A1/fr not_active Abandoned
- 2009-06-22 EP EP13003519.9A patent/EP2682388B1/fr not_active Revoked
- 2009-06-22 SI SI200931310T patent/SI2318365T1/sl unknown
- 2009-06-22 PT PT97698104T patent/PT2318365E/pt unknown
- 2009-06-22 ES ES09769810.4T patent/ES2552653T3/es active Active
- 2009-06-22 HR HRP20151208TT patent/HRP20151208T1/hr unknown
- 2009-06-22 EP EP09769810.4A patent/EP2318365B1/fr not_active Revoked
- 2009-06-22 WO PCT/IN2009/000357 patent/WO2009157018A2/fr not_active Ceased
- 2009-06-22 AU AU2009263737A patent/AU2009263737B2/en not_active Ceased
- 2009-06-22 HU HUE09769810A patent/HUE025982T2/en unknown
2014
- 2014-01-23 US US14/161,967 patent/US20140135504A1/en not_active Abandoned
2015
- 2015-07-29 US US14/812,053 patent/US9725412B2/en not_active Expired - Fee Related
- 2015-11-10 CY CY20151101010T patent/CY1116930T1/el unknown

Also Published As

Publication number	Publication date
DK2318365T3 (en)	2015-11-23
ES2552653T3 (es)	2015-12-01
EP2318365A2 (fr)	2011-05-11
HRP20151208T1 (hr)	2015-12-18
CA2729604C (fr)	2017-12-05
SI2318365T1 (sl)	2016-01-29
CA2919564A1 (fr)	2009-12-30
CY1116930T1 (el)	2017-04-05
US20140135504A1 (en)	2014-05-15
EP2682388A1 (fr)	2014-01-08
US8686161B2 (en)	2014-04-01
CA2729604A1 (fr)	2009-12-30
WO2009157018A3 (fr)	2010-07-29
WO2009157018A2 (fr)	2009-12-30
US20150336890A1 (en)	2015-11-26
AU2009263737B2 (en)	2013-10-24
PL2318365T3 (pl)	2016-02-29
PT2318365E (pt)	2015-11-25
EP2682388B1 (fr)	2018-01-10
WO2009157018A9 (fr)	2010-06-10
US20110301357A1 (en)	2011-12-08
EP2318365B1 (fr)	2015-08-12
AU2009263737A1 (en)	2009-12-30
US9725412B2 (en)	2017-08-08

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